Acetic Anhydride → HCID 58012320, compound

HRID 1698553Notes

Reaction equation

HRID 1698553 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10]2[N:14]([CH2:15][CH2:16][OH:17])[C:13]3[C:18]([C:22]([OH:29])([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])=[CH:19][CH:20]=[CH:21][C:12]=3[N:11]=2)=[C:4]([O:30][CH3:31])[CH:3]=1.[C:32](OC(=O)C)(=[O:34])[CH3:33]>N1C=CC=CC=1>[C:32]([O:17][CH2:16][CH2:15][N:14]1[C:13]2[C:18]([C:22]([OH:29])([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])=[CH:19][CH:20]=[CH:21][C:12]=2[N:11]=[C:10]1[NH:9][C:5]1[C:6]([CH3:8])=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[O:30][CH3:31])(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 58012444HCID 58012444, compound

Product 1

HCID 58012320HCID 58012320, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-[2-[(4-chloro-2-methoxy-6-methylphenyl)amino]-1-(2-hydroxyethyl)-1H-benzimidazol-7-yl]heptan-4-ol (100 mg, 0.22 mmol) in pyridine (5 mL) was treated with acetic anhydride (1 mL) and stirred at room temperature overnight. The reaction mixture was concentrated to dryness, diluted with aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on a silica gel to give 97 mg (0.20 mmol, 89%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additiondiluted with aqueous sodium hydrogen carbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on a silica gel

Sources & evidence

ORD record
ord-d961964cd40b41239904bcc011574030
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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